14:15 - Made a solution of 7.6143g vanillin and 31.0074g ethanol. Measured 4.6578g aniline in a vial.
14:18 - Added vanillin/ethanol solution to a 250mL erlenmeyer flask, slowly added aniline to the solution. Covered in parafilm and set on magnetic stirring plate. Solution is clear.
14:44 - Mixture is bright yellow and cloudy, chilled with water and ice.
14:51 - Filtered the mixture using a bΓΌchner funnel and house vacuum. Put the mixture in a vial with cap (mass of vial and cap is 13.8520g). Punctured cap of vial and set in desiccator under high vacuum.
2011-06-21
14:10 - Removed sample from desiccator (1A). Made a solution of the product and CDCl3. Added solution to NMR tube.
14:30 - Took HNMR using 300MHz varian NMR (HNMR-1A).
15:30 - Took some sample in a melting point capillary, started heating.
15:31 - Temperature is 30C (the following entries are all for the temperature on the thermometer of the melting point apparatus)
15:32 - 37C
15:33 - 46C
15:34 - 65C
15:35 - 90C
15:36 - 100C
15:37 - 99C
15:38 - 95C
15:39 - 98C
15:40 - 102C
15:41 - 103C
15:42 - 102C
15:43 - 105C
15:44 - 112C
15:45 - 115C
15:46 - 114.5C
15:47 - 116C
15:48 - 122C
15:49 - 126C
15:50 - 128C
15:51 - 129C
15:52 - 132C
15:53 - 136C
15:54 - 138C
15:55 - 140C
15:56 - 142C
15:57 - 145C
15:58 - 147C
15:59 - 151C [what is the melting point? JCB]
2011-06-22
12:11 - Put sample 1A into desiccator under high vacuum.
14:15 - Removed sample (now 1B) from desiccator.[report mass and add to sheet to get yield JCB]
14:20 - Added CDCl3 to some of the sample, transferred to NMR tube
14:34 - Took HNMR spectrum using 500MHz varian NMR (HNMR 1B).
14:52 - Put sample 1B into desiccator under high vacuum.
2011-06-23
13:47 - Removed sample (now 1C) from desiccator.
14:03 - Add CDCl3 to some of the sample, transferred to NMR tube.
14:25 - Took HNMR spectrum using varian 300MHz NMR (HNMR 1C).
Researcher
Evan CurtinObjective
To synthesize an imine from vanillin and aniline in order to collect solubility data.Procedure
Results
Exp268 Plan SheetCharacterization of 1A:
Characterization of 1B:
Characterization of 1C:
Discussion
Conclusion
Log
2011-06-20
14:15 - Made a solution of 7.6143g vanillin and 31.0074g ethanol. Measured 4.6578g aniline in a vial.14:18 - Added vanillin/ethanol solution to a 250mL erlenmeyer flask, slowly added aniline to the solution. Covered in parafilm and set on magnetic stirring plate. Solution is clear.
14:44 - Mixture is bright yellow and cloudy, chilled with water and ice.
14:51 - Filtered the mixture using a bΓΌchner funnel and house vacuum. Put the mixture in a vial with cap (mass of vial and cap is 13.8520g). Punctured cap of vial and set in desiccator under high vacuum.
2011-06-21
14:10 - Removed sample from desiccator (1A). Made a solution of the product and CDCl3. Added solution to NMR tube.14:30 - Took HNMR using 300MHz varian NMR (HNMR-1A).
15:30 - Took some sample in a melting point capillary, started heating.
15:31 - Temperature is 30C (the following entries are all for the temperature on the thermometer of the melting point apparatus)
15:32 - 37C
15:33 - 46C
15:34 - 65C
15:35 - 90C
15:36 - 100C
15:37 - 99C
15:38 - 95C
15:39 - 98C
15:40 - 102C
15:41 - 103C
15:42 - 102C
15:43 - 105C
15:44 - 112C
15:45 - 115C
15:46 - 114.5C
15:47 - 116C
15:48 - 122C
15:49 - 126C
15:50 - 128C
15:51 - 129C
15:52 - 132C
15:53 - 136C
15:54 - 138C
15:55 - 140C
15:56 - 142C
15:57 - 145C
15:58 - 147C
15:59 - 151C
[what is the melting point? JCB]
2011-06-22
12:11 - Put sample 1A into desiccator under high vacuum.14:15 - Removed sample (now 1B) from desiccator.[report mass and add to sheet to get yield JCB]
14:20 - Added CDCl3 to some of the sample, transferred to NMR tube
14:34 - Took HNMR spectrum using 500MHz varian NMR (HNMR 1B).
14:52 - Put sample 1B into desiccator under high vacuum.
2011-06-23
13:47 - Removed sample (now 1C) from desiccator.14:03 - Add CDCl3 to some of the sample, transferred to NMR tube.
14:25 - Took HNMR spectrum using varian 300MHz NMR (HNMR 1C).